2-Chloroaniline → HCID 22922546, compound

HRID 1081467Notes

Reaction equation

HRID 1081467 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[Cl:14][C:15]1[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=1N>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[Cl:14])[CH:3]=1

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 22922546HCID 22922546, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 101 g of 4-chloro-1,2-dinitrobenzene and 191 g of 2-chloroaniline in 750 ml of 95° EtOH is refluxed for 96 hours. The solvent is evaporated off under vacuum, the residue is extracted with DCM, washed with a 3 N solution of HCl and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/hexane mixture (50/50; v/v) as the eluent to give 7 g of the expected product after crystallization from EtOH. M.p.=97° C.

Workup

  1. temperatureis refluxed for 96 hours
  2. customThe solvent is evaporated off under vacuum
  3. extractionthe residue is extracted with DCM
  4. washwashed with a 3 N solution of HCl and with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using a DCM/hexane mixture (50/50; v/v) as the eluent

Sources & evidence

ORD record
ord-3309c214955b4fe5b8a4586adfcb1642
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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